Trying Something New
by Chelstiel Winchester
Summary: Dean decides to show Jack something new. The first portion of this fic comes from another author from AO3 and I continued their story and gave it an ending. Rated M for the entire fic! You've been warned!


"It's okay, Jack." Dean's voice is gentle as he spreads Jack's legs, kissing first his knee, and then the inside of his thigh. "It's okay to want this."

Jack stares up at him with heavy-lidded eyes, his toes curling into the mattress. "I - I do want this. Please, Dean." He arches his back, a soft sound escaping his kiss-swollen lips. "I read all the articles and everything..."

"Good boy," Dean praises, the words rolling off his tongue, as he uses that same tongue to flick out and touch Jack's hole.

Jack groans, his thighs closing around Dean's head. "Oh, my...G-God..."

"Yeah," Dean breathes, and he licks him fully now, the flat of his tongue enveloping the whole of that tiny ring of muscle.

Jack cries out, thrashing on the bed, his cock twitching against his belly. "Dean - oh. That's - that's so..."

"Hey, remember what I told you, sweetheart? You gotta be quiet, okay? You gotta keep it down. Don't want anyone to hear us." He seals his mouth around Jack's hole and sucks.

Jack's eyes widen, and he quickly crams his fist into his mouth so that he doesn't make any noise; he can feel Dean's tongue trying to work its way into him, and...

"U-Uh..." It's such a pathetic whimper, but it's all he can get out without being too loud.

Dean continues to eat him out, making the wettest, sloppiest noises, and...honestly, Jack can't hold it in anymore.

His stomach starts to twitch, his hole contracting around Dean's tongue, and...he's coming, gasping and twisting as he spills all over himself, the tight ball of his heat finally unfurling. "Dean, Dean, Dean..." He's chanting quietly, his body humming with satisfaction.

Dean pops up from between his legs, licking his lips. "Look at you, kid," he whispers, voice a little hoarse. "Came without me even touching your cock. Good boy." He stares down at Jack's hole, pink and slippery, and thumbs over it.

Jack whimpers, sensitive. "Dean - - what...what comes next?"

Dean smirks, kissing his way up Jack's body until he's sliding his tongue between those beautiful, full lips. "You again, if we're lucky."

"What about you?" Jack replies curiously.

"Me?" Dean raises a brow, amused. "Trust me, there's a hundred things I want to do to you right now. But I don't want to overwhelm you."

"But I want to be overwhelmed," Jack leans up on his elbows, looking into Dean's eyes. Dean notices that Jack's usual innocent expression has been replaced with a lust-filled smirk that makes his heart skip a beat. His gaze falters and he bites his lip, debating his next move. But Jack is a step ahead of him. He sits up and fumbles with Dean's belt. "I want to show you what else I learned from reading the articles."

"Oh, shit," Dean moans as he helps tug his jeans and boxers off. Jack kneels on the bed between Dean's legs as Dean pulls his shirt over his head and tosses it aside.

"First, I have to ask you. Is it ok if I touch you, Dean?" Jack tilts his head as he waited for Dean's compliance. Dean nods, looking him in the eye. "Ok." Jack nervously runs his hands over Dean's chest and abdomen, marveling at all the muscle he has. He pauses at Dean's overwhelming arousal, gaping at his size. He bends down and experimentally flicks his tongue slowly across the tip, making Dean gasp and shudder at the sudden pleasure. "Are you alright, Dean?" Jack asks as he wraps his hand around Dean's pulsing cock and begins stroking him.

"Y-yeah, fuck. Yeah. I like it," Dean closes his eyes, pressing his head back into the pillow with a groan. Jack smiles proudly. He's happy that he can pleasure Dean so easily. Dean's eyes flash open when he feels a sudden wet heat envelop his arousal. He growls and grabs Jack's hair in response, guiding his mouth at a pace he can handle. Jack hums, running his tongue around Dean's cock. "Fuck, Jack, uhhh…" Jack grips Dean's thighs as he continued sucking and teasing with his tongue. "Jack, _uhhh_, Jack. W-wait." Dean reluctantly pushes Jack off of him, and Jack sits up with a worried look.

"Did I do something wrong, Dean?"

"No, it was fucking perfect. But I want to show you something else…If you want me to…"

"Yes, Dean. I would very much like you to." Jack replies with a smile.

"Tell me if you feel uncomfortable, ok?"

"Ok."

Dean pushes Jack to lie back on the bed and gets down between his legs. He expertly flicks his tongue around Jack's hole, making the boy cry out in pleasure. After a moment, he slowly pushes a finger into Jack's entrance. Jack makes a new sound, and Dean pauses.

"You ok, sweetheart?"

"Y-yes. Please keep going." Jack replies quietly. Dean complies, and starts pumping his finger a bit faster before adding a second. Jack is groaning and writhing on the bed beneath him as Dean picks up the pace.

"Are you ready for me?" Dean asks, his voice deep with lust.

"Yes, Dean," Jack replies, peeking back at him over his shoulder. "Please fuck me."

Dean growls and grabs Jack's hips roughly, lining himself with the boy's entrance. He pushes in slowly, groaning through his teeth as Jack whimpers in pleasure. Dean pulls out a little before pushing in again, and starts thrusting slowly. He tries to be gentle, but Jack's moaning makes Dean lose control.

"Deannn_uhhh_…" Jack moans quietly.

"Louder." Dean demands.

"You t-told me I have to be qu-quiet…" Jack manages in between thrusts.

"Fuck it, I wanna hear you scream." Dean growls as he pounds faster and harder into Jack. Jack complies and moans louder, letting it all out. His throbbing cock is being pressed into the mattress with each thrust, aching for release.

"_Uhhh, Dean! _Fuck me harder, Daddy, _unhhhh,_" Jack yells, experimenting with the pet-name he read online. Dean wraps an arm around Jack's chest and pulls him to kneel up on the bed while still inside him. He grips Jack's aching cock and strokes him in time with his thrusts. "Yes…" Jack sighs in pure ecstasy. "Oh, Dean…"

"Yeah? You like that? Tell me…" Dean bites Jack's shoulder playfully.

"I-I like it. I'm gonna…I'm-"

"You gonna come, angel? Come for me," Dean gives Jack a sweet kiss on the side of his neck. Jack blushes hard at being called an angel. He feels so happy and proud that he's sharing this moment with Dean Winchester, he could burst.

"Y-yes. Please d-don't stop." Jack stutters as Dean continues stroking his cock and thrusting into him.

"Come, angel." Dean presses his lips against Jack's neck again, pushing further inside him and hitting his prostate, and that sends Jack over the edge.

"Oh-oh, g-_Dean_!" Jack comes hard, covering Dean's hand and some of the bedsheets. Dean is surprised he's lasted this long. He can feel himself getting close as Jack's entrance pulses around him. Jack lays down flat on his stomach, and Dean grabs Jack's hips, raising his ass in the air so he can pound into him easier. Jack peeks over his shoulder at Dean again, and suddenly his eyes glow golden. "Dean, come inside me…" Jack moans breathlessly, still coming down from his high. Dean suddenly feels his orgasm surge forward and almost knock him over.

"_Uhhh_, so fucking good. Ja-Jack, oh, _fuck_, Jack, _uhhhh_." Dean moans helplessly as Jack uses his powers to control Dean's orgasm. A power surge floods Dean's veins, and the burning heat of release builds up so much faster in his abdomen. "Fuck, I'm coming," he groans as he pushes as far in as he can go, riding it out.

He pulls out and collapses beside Jack on the bed. Jack rests his head in his hand and grins proudly at Dean, his hair all flustered and sticking to his forehead.

"Did you like it?" Dean asks in a hoarse voice after a moment of catching his breath.

"Yes, that was incredible, Dean." Jack's smile widens.

"Good, cuz I'm gonna pass out now." Dean's eyes flutter shut, his body exhausted after Jack's powers flowed through him.

"I will be ready to do it again when you wake up," Jack replies, lying back on the pillow beside Dean.

"I might be ready in a few weeks," Dean says as he dozes off.


End file.
